Holly, 1600 Block of N Wolcott Ave, Chicago, IL

Holly rides a '70s Schwinn Suburban called Penny.

Tell me more about bike, and where you got it?
My bike, Penny, is a '70s Schwinn Suburban. I spotted her years ago in a thrift store on the south side. I went back the next day at 6:00 am to get half off the price! I had the bike in storage until the folks at Boulevard Bikes installed new wheels, brake pads, a new chain and a basket. I don't often ride this bike, so it's great that you caught me today on Penny, my pretty parade bike. 
What are you wearing?
I'm pretty heavily layered because I plan to be out all day. I'm wearing a merino wool Icebreaker sweater under a vintage cashmere cardigan. This skirt is from one of my favorite indie fashion concerns, Made with Love By Hannah.  I have on a pair of tights under my Smartwool leggings,  red Vans, and a high-viz bicycling jacket. 
Why ride?
I can't imagine living in the city and not riding my bike. The first years I lived in Chicago, my bike sat in the basement. I used to work in the West Loop and was terrified of riding in Chicago. I didn't know how to dress, how to carry things, or how to make things easier by riding assertively or taking quiet streets.  Now, after nine years of riding anywhere and everywhere, my fear has subsided and I absolutely love being on my bike. I'm a dog walker. My daily dog walker route is a ten mile loop. Driving a car to walk the dogs is not at all efficient. It's a lot harder to deal with my car than just hopping on my bike. What's more, it makes me feel awesome!
While riding you...
I try to enjoy the scenery and relax, but I admit that sometimes I ride fast.  My other bike is a road bike and she loves to go fast, especially when we're headed to and from clients' houses. I know those streets like the back of my hand. Still--I'm intensely focused and alert.  Oh, and I always chew gum.
Favorite ride?
I love riding at night and in all seasons. The Chicago Bike Winter Group  has been really helpful and encouraging, and I've really developed an appreciation for winter riding. Lately, I've gotten involved with Chicago Critical Lass. That's a really fun ladies group ride.  You should come sometime!
How can Chicago improve bike infrastructure or make Chicago more bike friendly?
Ideally, fewer cars! In lieu of that, drivers need to understand that bikes have a place on the road. I get frustrated when some driver honks or treats me like I don't have a right to be on the street. There needs to be some mutual respect and maybe some re-education on defensive driving. Don't they teach that anymore? 
Check out Holly's amazing vintage clothing site.  I know I've got a few dresses from there on my Xmas list.
http://www.lucitebox.com